N1-carbamidomethyl-n2-(beta-hydroxyethyl) urea



United States Patent N -CARBAMIDOMETHYL-N -(B-HYDROXY- ETHYL) UREA Seymour L. Shapiro, Hastings on Hudson, and Louis Freedman, Bronxville, N.Y., assignors to US. Vitamin and Pharmaceutical Corporation, New York, N.Y., a corporation of Delaware No Drawing. Application December 29, 1958 Serial No. 783,204

1 Claim. (Cl. 260-553) This invention is concerned with N -carbamidornethyl- N -(p-hydroxyethyDurea which is a stable, water-soluble, crystalline compound of low toxicity with excellent antiinflammatory activity and as such is useful in human and veterinary medicine.

Example 1 2,921,091 Patented Jan. 12, 1960 A solution of the urea above, 4.0 g. (0.021 mole) in ml. of MeOH was saturated with ammonia, maintaining the internal temperature below 15 C. by external cooling. After storage for 72 hours at 20 C. the carbamido urea, 1.65 g., precipitated and recrystallized (ethanol), melted at 159-161" C.

Analysis.Calcd. for C H N O C, 37.3; H, 6.9; N, 26.1. Found: C, 37.8; H, 6.8; N, 26.4.

This was the product which had a minimum lethal dose of 750 mg./kg. subcutaneous in mice, and showed an anti-inflammatory activity of 15 units per gram (see Shapiro et al., I. Am. Pharm. Assoc, Sci. Ed. 46, 333 (1957), (for method of testing).

The novel compound of this invention can be combined with solid or liquid pharmaceutical carriers and formulated into the form of tablets, powder packets or capsules, or dissolved in suitable solvents for oral and parenteral administration for human or veterinary use.

It is to be understood that it is intended to cover all changes and modifications of the example herein chosen for the purpose of illustration 'which do not constitute departures from the spirit and scope of the invention.

We claim:

The compound 0 II II NHz-C-CHr-NH-C-NH-CHaCHnOH No references cited. 

